(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Base Information

Chemical Name:(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one
CAS No.:866021-67-2
Molecular Formula:C₃₅H₆₄O₆Si₂
Molecular Weight:637.061
Hs Code.:

(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Synonyms:(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

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Chemical Property of (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

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Technology Process of (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

There total 7 articles about (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 866021-64-9
(R)-3-(tert-butyldimethylsilanyloxy)-4-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}butyraldehyde

: 112763-31-2
(S)-4-benzyloxy-3-methyl-2-butanone

: 866021-67-2
(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

: (2S,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Guidance literature:: (S)-4-benzyloxy-3-methyl-2-butanone; With triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; at -78 ℃;

(R)-3-(tert-butyldimethylsilanyloxy)-4-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}butyraldehyde;

With pH 7 buffer; dihydrogen peroxide; In methanol; pH=7;
DOI:10.1021/ol051405x

Reference yield:

: 866021-62-7
((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester

: 866021-67-2
(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: PPh₃ / CH₂Cl₂

2.1: diethyl ether / -78 °C

3.1: LiAlH₄ / diethyl ether / -78 °C

4.1: imidazole; DMAP / dimethylformamide

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: PPh₃ / CH₂Cl₂

6.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

6.3: 87 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

With 1H-imidazole; dmap; lithium aluminium tetrahydride; ozone; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol051405x

Reference yield:

: 866021-79-6
[(2R,6S)-6-(2-oxoethyl)tetrahydropyran-2-yl]acetic acid ethyl ester

: 866021-67-2
(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / -78 °C

2.1: LiAlH₄ / diethyl ether / -78 °C

3.1: imidazole; DMAP / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: PPh₃ / CH₂Cl₂

5.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

5.3: 87 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

With 1H-imidazole; dmap; lithium aluminium tetrahydride; ozone; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol051405x